Pyrene

Manufactured by Thermo Fisher Scientific

Sourced in United States

Pyrene is a polycyclic aromatic hydrocarbon (PAH) that is commonly used as a fluorescent probe and molecular probe in various analytical and research applications. It has a distinct fluorescence emission spectrum that can be utilized for studying molecular interactions, conformational changes, and other phenomena in chemical and biological systems.

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15 protocols using pyrene

Synthesis and Characterization of Pyrogallol[4]arene Compounds

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Reagents, solvents, guest molecules, and synthetic precursors were purchased from commercial suppliers at ACS Reagent Grade or equivalent purity and used without further purification. Pyrogallol, butrylaldehyde, anthracene, fluoranthene, pyrene, and fluorene were obtained from Acros Organics. Hydrochloric acid, ethanol, and methanol were obtained from Fisher Scientific. Undecanal and 1,5-diaminonaphthalene were obtained from TCI. Carbazole and coumarin were obtained from Sigma-Aldrich. 1-Adamantanecarboxylic acid and [2.2]paracyclophane were obtained from Alfa Aesar and Combi-blocks respectively. Deuterated solvents for NMR spectroscopy were purchased from Cambridge Isotopes. CDCl₃ was filtered through basic alumina prior to use. Pyrogallol[4]arenes 1a and 1b were synthesized using published procedures.26 ,32
¹H and ¹³C solution NMR spectra were acquired using a Bruker Avance IIIHD 600 MHz, a Varian Unity INOVA 500 MHz, or a Varian Mercury 400 MHz spectrometer. Residual solvent peaks were used as internal standards: CHCl₃ (δ^H = 7.26 ppm; δ^C = 77.16 ppm), benzene (δ^H = 7.16 ppm; δ^C = 128.06 ppm). NMR measurements performed in CCl₄ used a coaxial NMR tube insert and C₆D₆ for an external solvent lock and chemical shift referencing.

Journey S.N., Teppang K.L., Garcia C.A., Brim S.A., Onofrei D., Addison J.B., Holland G.P, & Purse B.W. (2017). Mechanically induced pyrogallol[4]arene hexamer assembly in the solid state extends the scope of molecular encapsulation †Electronic supplementary information (ESI) available: Experimental procedures, NMR spectra, and tabulated data. See DOI: 10.1039/c7sc03821f. Chemical Science, 8(11), 7737-7745.

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Organic-free Sediment Characterization

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The natural sediment was collected from the top 0–20 cm of the sediment in Lanzhou Reach of the Yellow River. It was washed using double distilled water, air-dried, and sieved to obtain the size fraction of 38–75 μm. H₂O₂ treatment was performed to obtain the organic-free sediment according to Kunze and Dixon [13 ], followed by the steps of washing, drying, and sieving. The same size fraction as the natural sediment was used for the experiment. Kaolinite (a product of inorganic clay) was purchased from Fuchen Chemical Reagent Co., Inc. (Tianjin, China) and was used without further treatment.
Phenanthrene and pyrene were purchased from Acros Organics (New Jersey, USA). NP was purchased from Tokyo Chemical Synthesis Ind. Co. Ltd (Tokyo, Japan). They were dissolved in methanol to make their respective stock solution. Humic acid (HA) was purchased from Tianjin Guangfu Fine Chemical Research Institute in China, which was dissolved in 0.1 mM NaOH solution and filtrated through a 0.45 μm membrane to obtain a stock solution (0.89 g/L).

Wu Y., Liu F., Zhang W, & Wang L. (2014). Effect of Cosolutes on the Sorption of Phenanthrene onto Mineral Surface of River Sediments and Kaolinite. The Scientific World Journal, 2014, 812531.

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Soil Contamination by Model PAHs

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Four organic compounds, naphthalene (B&K Multi-branch Company), phenanthrene, anthracene, and pyrene (Acros Organics), were used as the model PAHs in the experiment. All of the tested compounds have been designated as priority pollutants by the US Environmental Protection Agency (US EPA). Soil samples were contaminated with powdered PAHs in the amount of 0, 1000, 2000, and 4000 mg kg⁻¹ dry matter of soil. The application of such high doses was justified by the amounts of PAHs that are released into the soil environment as a result of frequent and uncontrolled spills of petroleum derivatives (Park and Park 2011 (link)). Naphthalene, phenanthrene, anthracene, and pyrene are characterized by n-octanol/water partition coefficients of 3.6, 4.46, 4.5, and 4.8, respectively; they are insoluble in water, but soluble in organic compounds.

Lipińska A., Wyszkowska J, & Kucharski J. (2015). Diversity of organotrophic bacteria, activity of dehydrogenases and urease as well as seed germination and root growth Lepidium sativum, Sorghum saccharatum and Sinapis alba under the influence of polycyclic aromatic hydrocarbons. Environmental Science and Pollution Research International, 22(23), 18519-18530.

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Polycyclic Aromatic Hydrocarbon Synthesis

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Brij 30 (polyoxyethylene (4) lauryl ether) and polyoxyethylene sorbitol hexaoleate (POESH) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Phenanthrene (98%) and chrysene (98%) were also purchased from Sigma-Aldrich. Pyrene (98%) was purchased from Acros Organics (Thermo Fisher Scientific, Waltham, MA, USA).

Singleton D.R., Adrion A.C, & Aitken M.D. (2016). Surfactant-induced bacterial community changes correlated with increased polycyclic aromatic hydrocarbon degradation in contaminated soil. Applied microbiology and biotechnology, 100(23), 10165-10177.

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Synthesis and Characterization of Pyrene-Functionalized Polypeptides

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Pyrene and γ-benzyl-l-glutamic acid ester were used as received from Acros. Palladium on carbon (Pd/C, 10 wt%), 4-fluoronitrobenzene, hydrazine hydrate (98%), triphosgene, and potassium carbonate were obtained from Alfa Aesar. Glacial acetic acid was purchased from Fluka. Ethanol (EtOH), dimethylsulfoxide (DMSO), methanol (MeOH), THF, and acetonitrile were obtained from Merck and distilled over CaH₂ prior to use. MWCNTs [diameters (main range): 40–60 nm; lengths: 5–15 μm] were ordered from Centron Biochemistry Technology (Taiwan). MWCNTs were purified through sonication in toluene for 1 h, ultrafiltration, and drying under vacuum overnight. BLG-NCA^{45 (link)} and 1-aminoPyrene^{46 (link)} were synthesized using previously reported methods.

EL-Mahdy A.F, & Kuo S.W. (2018). Diphenylpyrenylamine-functionalized polypeptides: secondary structures, aggregation-induced emission, and carbon nanotube dispersibility. RSC Advances, 8(28), 15266-15281.

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Synthesis of Pyrene-Labeled Polymer Prodrug

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Epsilon-caprolactone (ε-CL), N,N’-dicyclohexyl carbodiimide (DCC), succinic anhydride, and pyrene were purchased from Acros Organics (Geel, Belgium). 5’-DFUR was obtained from TCI (Tokyo, Japan). Tetrahydrofuran (THF), toluene, dichloromethane (DCM), dimethyl sulfoxide (DMSO), deuterated dimethyl sulfoxide (DMSO-d₆), CDCl₃ with 1% tetramethylsilane (TMS), Sn(Oct)₂, hexane, N-Hydroxysuccinimide (NHS), acetone, pyridine, magnesium sulfate, 2-propanol, methanol, hydrochloric acid (HCl), SN-38, DOX, methoxypolyethylene glycol amine (MPEG-NH₂; MW = 5000), MPEG (MW = 350), penicillin-streptomycin, 0.25% trypsin/EDTA, RIPA lysis and extraction buffer, protease inhibitor, thymidine, thymine and 5-fluorouracil were all purchased from Sigma-Aldrich (St. Louis, MO, USA). HT-29 colorectal cell line was purchased from ATCC (HTB-38, Manassas, VA, USA). Fetal bovine serum (FBS) was purchased from Atlanta Biologicals (Flowery Branch, GA, USA). Dulbecco’s modified Eagles’ medium (DMEM) was purchased from Corning Cellgro (Manassas, VA, USA). Potassium phosphate and sodium hydroxide were purchased from Fisher Scientific (Fair Lawn, NJ, USA).

Sawdon A.J., Zhang J., Wang X, & Peng C.A. (2018). Enhanced Anticancer Activity of 5’-DFUR-PCL-MPEG Polymeric Prodrug Micelles Encapsulating Chemotherapeutic Drugs. Nanomaterials, 8(12), 1041.

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Multifunctional Nanocarrier Synthesis

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Bis(2-hydroxyethyl) disulfide, 1,1,4,7,10,10-hexamethyltriethylenetetramine (HMTETA), copper (I) bromide (CuBr), iron (III) acetylacetonate (Fe(acac)₃), oleic acid, tri-octylamine, DOX, (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride) (EDC), N-hydroxysuccinimide (NHS) and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide (MTT) were purchased from Sigma. Amberlite^® IR120, 2-bromo-2-methylpropionyl bromide, CL, rhodamine 123 (R123), GSH and pyrene were purchased from Acros. Neutral aluminium oxide (Al₂O₃) was purchased from Seedchem Company. Tin (Ⅱ) 2-ethylhexanoate (Sn(Oct)₂) and o-phenylenediamine were purchased from Alfa Aesar. Dithiothreitol (DTT) was purchased from J.T. Baker. Tert-butyl methacrylate (tBMA) and trimethylamine (TEA) were purchased from TCI. Polyvinyl alcohol (PVA, MW=2000) was purchased from Showa. Minimum essential medium, penicillin, streptomycin and fetal bovine serum (FBS) were purchased from Biological Industries. The annexin-V/PI staining kit was purchased from Strong Biotech Corporation. Dulbecco’s modified Eagle’s medium (DMEM) was purchased from Invitrogen.

Tsai M.F., Lo Y.L., Huang Y.C., Yu C.C., Wu Y.T., Su C.H, & Wang L.F. (2020). Multi-Stimuli-Responsive DOX Released from Magnetosome for Tumor Synergistic Theranostics. International Journal of Nanomedicine, 15, 8623-8639.

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PAHs Extraction and Analysis

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Four EPA-priority PAHs were used in this study. Fluorene and pyrene were purchased from Acros Organics, and chrysene and benzo[a]pyrene from Sigma-Aldrich. ABTS and MBTS were acquired from Alfa Aesar. DMAB was obtain from Sigma-Aldrich, and acetonitrile (HPLC grade) and polyvinylpolypyrrolidone were purchased from Fisher Scientific.

Vipotnik Z., Michelin M, & Tavares T. (2021). Ligninolytic enzymes production during polycyclic aromatic hydrocarbons degradation: effect of soil pH, soil amendments and fungal co-cultivation. Biodegradation, 32(2).

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Purification and Characterization of Fluorinated Surfactants

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All fluorinated surfactants, apart from sodium perfluorooctanoate (NaPFO), used in this study were provided by commercial suppliers (see below). Dynax TM DX1030 is a C6 anionic fluorosurfactant (IUPAC Name:
propan-1-aminium) Dynax TM is a trademark of Dynax Corporation and Capstone TM is a trademark or The Chemours Company. Technical grade surfactants were provided as liquid formulations, acetone was added as a non-solvent to induce precipitation of the solid surfactants for purification. Characterisation and chemical analysis were used to access purity of the precipitated FC surfactants (supporting information), showing the chemical compositions and spectral properties to be consistent with expected molecular structures. NaPFO (CAS 335-95-5) was prepared and purified by the following method. Perfluorooctananoic acid (CAS 335-67-1) of stated purity P99 % was obtained from Fluorochem, coverted into the appropriate metal salt by reaction with the stoichiometric amount of sodium hydroxide, and purified by recrystallisation from a mixture of ethanol and propanol (1:1, vol:vol). Further purification included Soxhlet extraction, with ethyl acetate as solvent, to remove residual inorganic material, and foam fractionation to remove hydrophobic impurities (following method in Ref. [17] ). Pyrene (Acros, puriss P99 %), deuterium oxide (Aldrich, 99.9 %) were used as received.

Hill C., Czajka A., Hazell G., Grillo I., Rogers S.E., Skoda M.W.A., Joslin N., Payne J, & Eastoe J. (2018). Surface and bulk properties of surfactants used in fire-fighting. Journal of colloid and interface science, 530.

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Cytotoxicity Assays Using Common Lab Reagents

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Dexamethasone (Sigma-Aldrich), methylprednisolone sodium succinate (Metypred, OrionPharma) and methylprednisolone (Medrol, Pfizer) were used. 3-(4,5-dimethyl-thiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), 2',7'-dichlorofluorescin diacetate, Triton X100, phenylmethanesulfonyl fluoride (PMSF), menadione sodium bisulfite were produced by Sigma-Aldrich. Pyrene, chromium (VI) oxide, reagents/solvents for chemical synthesis, and inorganic salts were purchased from Acros Organics. Hypergrade acetonitrile for LC-MS and formic acid were purchased from Merck Millipore.
Materials for cell culturing were obtained from PAA Laboratories. Milli-Q grade water (Milli-Q Advantage A10, Merck Millipore) was used to prepare buffers and solutions.

Kamalov M.I., Đặng T., Petrova N.V., Laikov A.V., Luong D., Akhmadishina R.A., Lukashkin A.N, & Abdullin T.I. (2018). Self-assembled nanoformulation of methylprednisolone succinate with carboxylated block copolymer for local glucocorticoid therapy. Colloids and surfaces. B, Biointerfaces, 164.

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